5 Songs from Crazy Ex-Girlfriend That Made Up the Soundtrack of My 20s

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I instantly fell in love with Crazy Ex-Girlfriend when it first premiered in October 2015. I was an early adopter to the show; I had heard all about its development process on Scriptnotes, John August and Craig Mazin’s screenwriting podcast that regularly features CEG showrunner Aline Brosh McKenna. It sounded like everything I ever wanted from a TV show - a raunchy musical romantic comedy starring a digital native - and more than lived up to the hype. I quickly became an evangelist for all things CEG and Rachel Bloom.

From the first few minutes of the pilot, I saw so much of myself in Bloom’s character, Rebecca Bunch. She’s someone who is so clearly struggling with her mental health, but still has the capacity for optimism and the ability to dream big, even if those dreams are sometimes misguided. Finally, here was someone on my TV who embodied the same kind of high-functioning mental illness that I’ve lived with my entire life. I usually roll my eyes when people point out the relatable bits in TV shows or movies that they think only apply to them (everyone’s been ghosted, Karen), but I found myself saying “Wow, so me” at least five times an episode.

The show wraps up tonight after four great seasons, and I’ve been thinking about how I’ve personally changed over that time. I’ve been through one job change, a big break up, several situationships, and countless internal crises in the last three and a half years. Hell, I almost packed up and moved to the west coast myself at one point during the show’s run. Through it all, though, CEG has been my constant. The show seems to have a song for almost everything I’m going through, a perk of watching a show about someone in her 20s when you’re in 20s. Here are just five CEG songs that have made up the soundtrack of the last few years of my life.

“Heavy Boobs”

I’ve had what Rebecca describes as “Heavy Boobs” since puberty, but it took me until well into my 20s to feel comfortable with said gifts. They always felt kind of awkward on my small frame, attracted more attention than I actually wanted, and severely limited my sartorial options (shopping for button-downs is my personal hell). But part of growing up is becoming more comfortable in your body. I won’t lie, that’s so much easier to do that when your body type is well-represented in the media. Rebecca is the lead character on a network TV comedy with a successful career, multiple romantic interests, and a dress size above a 2. It may not be groundbreaking but it’s been incredibly good to see.

“Don’t Be a Lawyer”

There was a time when I really thought I was going to go to law school. It’s kind of the obvious step for a good student with lots of experience with contracts, strong verbal skills, and a successful lawyer dad, right? Of course when I thought about actually taking the LSATs, going to law school and, you know, being a lawyer, none of it excited me. This song dropped a few months ago and I immediately knew I made the right choice not to pursue a legal career. No, I don’t think all lawyers are sad, but this song makes it clear that going to law school when you’re not really sure what to do with your life is probably not the best move. Plus, it’s a certified bop. This song also comes at a time when Rebecca realizes that, though she’s a very talented lawyer, she has no passion for it. Her journey to find a career that works for her looks a lot like my own (although I’ve yet to start my own pretzel shop), and makes me feel a lot less alone as I figure things out. And yes, I have sent this video to my dad.

“Oh My God I Think I Like You”

This is a song that has popped into my head on more than one occasion when I’ve found myself in a casual relationship that has become less emotionally casual (for me, at least). Oxytocin is a hell of a drug and sometimes it causes you to imagine yourself getting married on a rowboat surrounded by ducks to a person you’ve never really seen outside of your (or their) apartment! Of course, it all hits you even harder when you’re single for the first time in your adult life and trying to navigate dating in a city like New York. At least now I have a musical method for sorting out the terrifying business that is catching feelings.

“I Have Friends”

This short and sweet call-off bop might as well be sung by Young Charlotte and Current Charlotte. I’m lucky to have a lot of great friends, but making and maintaining friendships has always been a bit of a challenge. Attempting to make connections after college in a new city definitely made me feel like my awkward middle school self again, trying to convince myself that I did, indeed, have friends when in reality I felt very much alone. Thankfully, I’m feeling a lot more secure in my friendships now, but those first few years of trying to create a friend group out of nothing were pretty rough.

“(Tell Me I’m Okay) Patrick”

First off, this gem from Season 2 is extremely slept on. You get a good nostalgia hit with the Seth Green cameo and some excellent vocals from Bloom. And who hasn’t spilled their guts to a stranger in search of some kind of validation that they’re actually doing fine? No? Just me? Deep in my brain I know that I’m okay, but my anxious brain needs to be reminded of that sometimes. And I too feel like I missed the day in school where they taught everyone how to be a real person. But clearly that day never happened because a lot of other people feel like they missed out as well. I mean, there’s a whole song about it!


I will miss this show with every fiber of my being. We live in the age of Peak TV, so I know another show will come around that will speak to me the same way CEG did. If I’m lucky, I’ll even get to write that show. But tonight I’ll be celebrating four incredible seasons of the best show on TV and my own messy, wonderful mid-20s with some boba and a giant mall pretzel (or maybe just wine and popcorn, the mall pretzel will probably get cold on the subway and who wants that).

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